Angiomatous tumours of the skeletal system are rare in long bones but relatively more common in the axial bones. The updated 2020 WHO classification of soft tissue and bone tumours has introduced several streamlined revisions. Primary skeletal tumours have distinct aggressive and non-aggressive radiological appearances which help to differentiate them from one another. Analysis of immunohistochemistry and histomorphology aids in their definite diagnosis after bone biopsy. Benign lesions such as haemangiomas of the spine are easy to diagnose but every radiologist should remain vigilant of the intermittently locally aggressive lesions like epithelioid haemangioendotheliomas as well as haematologically metastasising angiosarcomas. This chapter covers these different tumours in detail with a focus on their radiological and pathological appearances. This chapter also highlights several rare syndromic associations of angiomatous lesions of the bone.